These are two different levels of play, the olympics are obviously the olympics the elite hockey players from each country that participates in hockey every 4 years battle for the gold medal, meaning they're the best team in the world. On the other hand the Stanley Cup is restricted to only players in the NHL although a majority of players in the league are from a foreign country, meaning there are few Americans in a mainly American league. Plus the olympic hockey championship happens once every 4 years compared to the Stanley Cup being every year at the end of each NHL season, so imo winning the Olympic gold medal for hockey would be a much higher honor then the Stanley Cup, although it would be pretty awesome to hoist the cup.